[ CAS No. 5344-90-1 ] {[proInfo.proName]}

Name: 5344-90-1|(2-Aminophenyl)methanol|98%
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SKU: A102134
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Quality Control of [ 5344-90-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5344-90-1 ]

Product Details of [ 5344-90-1 ]

CAS No. :	5344-90-1	MDL No. :	MFCD00007749
Formula :	C₇H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VYFOAVADNIHPTR-UHFFFAOYSA-N
M.W :	123.15	Pubchem ID :	21439
Synonyms :	(2-Aminophenyl)methanol;2-Hydroxymethylaniline

Calculated chemistry of [ 5344-90-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	36.97
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.34
Log Po/w (XLOGP3) :	-0.05
Log Po/w (WLOGP) :	0.62
Log Po/w (MLOGP) :	0.88
Log Po/w (SILICOS-IT) :	0.98
Consensus Log Po/w :	0.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.0
Solubility :	12.3 mg/ml ; 0.1 mol/l
Class :	Very soluble
Log S (Ali) :	-0.47
Solubility :	41.7 mg/ml ; 0.338 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.82
Solubility :	1.86 mg/ml ; 0.0151 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 5344-90-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5344-90-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 5344-90-1 ]
Downstream synthetic route of [ 5344-90-1 ]

[ 5344-90-1 ] Synthesis Path-Upstream 1~19

1
[ 5344-90-1 ]
[ 21352-22-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 9, p. 2073 - 2078

2
[ 5344-90-1 ]
[ 109-86-4 ]
[ 6931-17-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 37, p. 9570 - 9574

3
[ 5344-90-1 ]
[ 883-39-6 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 7, p. 2003 - 2005

4
[ 129249-75-8 ]
[ 5344-90-1 ]
[ 1131-94-8 ]

Reference： [1] Journal of the Indian Chemical Society, 1989, vol. 66, # 8-10, p. 673 - 680

5
[ 5344-90-1 ]
[ 552-16-9 ]
[ 612-25-9 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 72, p. 38446 - 38449

6
[ 5344-90-1 ]
[ 5159-41-1 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 1734 - 1747

7
[ 5344-90-1 ]
[ 40400-13-3 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 1734 - 1747

8
[ 5344-90-1 ]
[ 68-12-2 ]
[ 6526-66-5 ]

Reference： [1] Inorganic Chemistry, 2017, vol. 56, # 17, p. 10596 - 10608

9
[ 5344-90-1 ]
[ 616-38-6 ]
[ 29055-08-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	for 12 h;	Example 5 N-methyl-o-aminobenzyl alcohol A mixture of o-aminobenzyl alcohol (1 g) in DMC (30 ml) is prepared according to the method described in example 1. The two compounds are made to react in the presence of NaY-faujasite (1 g) for 12 hours in the conditions described in the preceding examples. The yield on the isolated title product is 92percent. The mono-N-methylation selectivity is 99percent.

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7374 - 7378
[2] Patent: US2004/127747, 2004, A1, . Location in patent: Page 4
[3] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2476 - 2485

10
[ 5344-90-1 ]
[ 141814-27-9 ]
[ 29055-08-1 ]
[ 4707-56-6 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2476 - 2485

11
[ 5344-90-1 ]
[ 29055-08-1 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 20, p. 3549 - 3551

12
[ 5344-90-1 ]
[ 616-38-6 ]
[ 29055-08-1 ]
[ 4707-56-6 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2476 - 2485

13
[ 5344-90-1 ]
[ 89942-45-0 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 583
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 372

14
[ 5344-90-1 ]
[ 77242-30-9 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1933, vol. <4> 53, p. 330,332

15
[ 5344-90-1 ]
[ 96-09-3 ]
[ 50-00-0 ]
[ 141-43-5 ]
[ 21535-47-7 ]

Reference： [1] Patent: CN108250203, 2018, A, . Location in patent: Paragraph 0009

16
[ 5344-90-1 ]
[ 20712-12-3 ]

Yield	Reaction Conditions	Operation in experiment
72.5%	With N-Bromosuccinimide In N,N-dimethyl-formamide for 2 h; Cooling with ice	To the reaction flask was added anthranilic alcohol (5.00 g, 40.0 mmol, commercially available), DMF (25 ml) was stirred at ice bath was added portionwise NBS (7.23 g, 40.0 mmol), the ice bath for 2 hours the reaction stirring the reaction solution was directly poured into ice water, filtered, washed and dried to obtain a white solid 5.86 g, yield 72.5percent.
72.5%	With N-Bromosuccinimide In N,N-dimethyl-formamide for 2 h; Cooling with ice	Dissolve o-aminobenzyl alcohol (5.00 g, 40.0 mmol, commercially available) in 25 mL DMF.NBS (7.23 g, 40.0 mmol) was added in portions with ice-bath stirring.After 2 hours of ice bath reaction, the reaction solution was poured directly into ice water with stirring.filter,washing,dry,5.86 grams of white solidYield 72.5percent.

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 39, p. 6965 - 6968
[2] Patent: CN105732587, 2016, A, . Location in patent: Paragraph 0111; 0112; 0113
[3] Patent: CN104650038, 2018, B, . Location in patent: Paragraph 0123; 0124; 0125

17
[ 52727-57-8 ]
[ 5344-90-1 ]
[ 20712-12-3 ]

Reference： [1] Organic letters, 2001, vol. 3, # 26, p. 4217 - 4220
[2] Organic letters, 2001, vol. 3, # 26, p. 4217 - 4220

18
[ 5344-90-1 ]
[ 20244-61-5 ]
[ 20712-12-3 ]

Reference： [1] Patent: US2002/151504, 2002, A1,
[2] Patent: US5843972, 1998, A,

19
[ 5344-90-1 ]
[ 158577-01-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 1, p. 29 - 39
[2] Heterocycles, 2000, vol. 53, # 11, p. 2471 - 2485
[3] Heterocycles, 2000, vol. 53, # 11, p. 2471 - 2485
[4] Patent: US2008/287486, 2008, A1,

[ 5344-90-1 ] Synthesis Path-Downstream 1~88

1
[ 5344-90-1 ]
[ 89942-45-0 ]

Reference： [1]Archiv der Pharmazie,1929,p. 583

2
[ 5344-90-1 ]
[ 816-39-7 ]
2,2-bis(bromomethyl)-1,4-dihydro-2H-3,1-benzoxazine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1980,vol. 99,p. 206 - 212

3
[ 5344-90-1 ]
[ 150374-99-5 ]
2,2-Dimethyl-propionic acid 4-(2-hydroxymethyl-phenylsulfamoyl)-phenyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2115 - 2134

4
[ 5344-90-1 ]
[ 20712-12-3 ]

Yield	Reaction Conditions	Operation in experiment
72.5%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 2h;Cooling with ice;	To the reaction flask was added anthranilic alcohol (5.00 g, 40.0 mmol, commercially available), DMF (25 ml) was stirred at ice bath was added portionwise NBS (7.23 g, 40.0 mmol), the ice bath for 2 hours the reaction stirring the reaction solution was directly poured into ice water, filtered, washed and dried to obtain a white solid 5.86 g, yield 72.5percent.
72.5%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 2h;Cooling with ice;	Dissolve o-aminobenzyl alcohol (5.00 g, 40.0 mmol, commercially available) in 25 mL DMF.NBS (7.23 g, 40.0 mmol) was added in portions with ice-bath stirring.After 2 hours of ice bath reaction, the reaction solution was poured directly into ice water with stirring.filter,washing,dry,5.86 grams of white solidYield 72.5percent.

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6965 - 6968
[2]Patent: CN105732587,2016,A .Location in patent: Paragraph 0111; 0112; 0113
[3]Patent: CN104650038,2018,B .Location in patent: Paragraph 0123; 0124; 0125

5
[ 52727-57-8 ]
[ 5344-90-1 ]
[ 20712-12-3 ]

Reference： [1]Organic letters,2001,vol. 3,p. 4217 - 4220
[2]Organic letters,2001,vol. 3,p. 4217 - 4220

6
[ 5344-90-1 ]
[ 104619-51-4 ]
[ 121743-54-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 191 - 193

7
[ 5344-90-1 ]
[ 616-38-6 ]
[ 29055-08-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	for 12h;	Example 5 N-methyl-o-aminobenzyl alcohol A mixture of o-aminobenzyl alcohol (1 g) in DMC (30 ml) is prepared according to the method described in example 1. The two compounds are made to react in the presence of NaY-faujasite (1 g) for 12 hours in the conditions described in the preceding examples. The yield on the isolated title product is 92percent. The mono-N-methylation selectivity is 99percent.

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 7374 - 7378
[2]Patent: US2004/127747,2004,A1 .Location in patent: Page 4
[3]Journal of Organic Chemistry,2005,vol. 70,p. 2476 - 2485

8
[ 5344-90-1 ]
[ 141814-27-9 ]
[ 29055-08-1 ]
[ 4707-56-6 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 2476 - 2485

9
[ 5344-90-1 ]
[ 616-38-6 ]
[ 29055-08-1 ]
[ 4707-56-6 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 2476 - 2485

10
[ 5344-90-1 ]
[ 932-16-1 ]
[ 83036-88-8 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 8988 - 9001

11
[ 5344-90-1 ]
[ 51310-54-4 ]

Reference： [1]Journal of Fluorine Chemistry,2007,vol. 128,p. 1143 - 1152

12
[ 5344-90-1 ]
[ 29055-08-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 3549 - 3551

13
[ 5344-90-1 ]
[ 33588-64-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 1193 - 1202
[2]Patent: US2011/98311,2011,A1
[3]Patent: US2015/231142,2015,A1

14
[ 5344-90-1 ]
potassium hydroxide [ No CAS ]
[ 103029-75-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 1533 - 1536

15
[ 5344-90-1 ]
potassium hydroxide [ No CAS ]
[ 4264-35-1 ]

Reference： [1]Chemische Berichte,1986,vol. 119,p. 2069 - 2074

16
[ 5344-90-1 ]
potassium hydroxide [ No CAS ]
[ 33588-64-6 ]

Reference： [1]Chemische Berichte,1986,vol. 119,p. 2069 - 2074

17
[ 5344-90-1 ]
[ 20244-61-5 ]
[ 20712-12-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	Example 3 Preparation of Compound 3.1 To a solution of 2-aminobenzyl alcohol (7.12 g, 58 mmol) in methylene chloride (200 mL) at -10° C., 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one (25 g, 61 mmol) was added in portions. During the addition, the temperature of the reaction mixture was maintained between -10° C. and 0° C. The reaction mixture was warmed up to room temperature and then extracted with 2 N sodium hydroxide solution (2*50 mL). The organic layer was washed with water and dried over MgSO4, filtered and concentrated in vacuo to afford 2-amino-5-bromobenzylalcohol as a yellow solid which was used without further purification.
		A. 2-Amino-5-bromobenzyl alcohol (1a): A solution of 12.316 g (0.1 mol) of 2-aminobenzyl alcohol in 300 mL of dry ether was treated at about 0° C. with 40.97 g (0.1 mol) of 2,4,4,6-tetrabromocyclohexa-2,5-dienone added in portions with vigorous stirring. Stirring was continued for about 1 hour at about 0° C., then the mixture was extracted twice with dilute HCl. The combined acid extracts were washed with ether and the ether was discarded. The acid solution was made alkaline with NaOH and extracted with fresh ether. The ether extracts were washed with water, brine, dried (Na2 SO4) and concentrated to afford 17.86 g (88percent) of 1a, mp 107-110° C. 1 H NMR (CDCl3): d=7.22-7.17 (m, 2 H); 6.57 (d, 1 H); 4.61 (s, 2 H). (MS (El): m/z=201, 203 (M+, Br isotopes).

Reference： [1]Patent: US2002/151504,2002,A1
[2]Patent: US5843972,1998,A

18
[ 5344-90-1 ]
[ 95104-21-5 ]
(2E,Z₄E)-N-Isobutyl 3-methyl-12-(3-cyano-2-quinolinyloxy) dodeca-2,4-dienamide [ No CAS ]
[ 529-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese dioxide; In chloroform;	EXAMPLE XIII Compound 30 (2E,Z4E)-N-Isobutyl 3-methyl-12-(3-cyano-2-quinolinyloxy) dodeca-2,4-dienamide Starting from <strong>[95104-21-5]2-chloro-3-cyanoquinoline</strong>. 2-Aminobenzyl alcohol (ex. Aldrich) (2 g) was oxidised with activated manganese dioxide (2.7 g) in chloroform over 20 hours. After filtration and concentration the crude product was purified by column chromatography on silica (ethyl acetate) to give 2-aminobenzaldehyde (1.9 g) as a dark-red oil which was used directly.

Reference： [1]Patent: US5114940,1992,A

19
[ 5344-90-1 ]
[ 15933-07-0 ]
[ 15785-08-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 8608 - 8611

20
[ 5344-90-1 ]
[ 4388-56-1 ]
C₁₃H₁₇NO₄ [ No CAS ]

Reference： [1]Synthesis,2008,p. 3846 - 3856

21
[ 5344-90-1 ]
[ 4506-45-0 ]
[ 1160479-69-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2010,vol. 46,p. 106 - 116

22
[ 5344-90-1 ]
[ 153813-70-8 ]
C₁₃H₁₃N₃O₃ [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1060 - 1063

23
[ 5344-90-1 ]
[ 153813-70-8 ]
[ 1266122-25-1 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1060 - 1063

24
[ 5344-90-1 ]
[ 6587-24-2 ]
[ 35970-06-0 ]

Reference： [1]Synlett,2011,p. 844 - 848

25
[ 5344-90-1 ]
[ 10075-49-7 ]
C₁₇H₁₇BrN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With trifluoroacetic acid; In 1,2-dichloro-ethane; at 20 - 50℃;Inert atmosphere;	General procedure: To a solution of 1 (0.28 mmol, 0.040 g) and 2 (0.14 mmol, 0.017 g) in DCE (0.41 mL) was added TFA (0.041 mmol, 0.0031 mL) at rt. The resulting solution was stirred at 50 C overnight. The reaction was quenched with saturated aqueous NaHCO3 (5.0 mL) and diluted with EtOAc (5.0 mL). The organic phase was washed with brine (10 mL), and then dried over Na2SO4. Solvent was removed using a rotary evaporator, and the residue was purified by silica gel chromatography (EtOAc/pentanes).

Reference： [1]Tetrahedron,2011,vol. 67,p. 4327 - 4332

26
[ 5344-90-1 ]
[ 99-90-1 ]
[ 24641-31-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With [(eta5-C5Me5)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)]OTf2; potassium hydroxide; In water; for 12h;Reflux; Green chemistry;	Bromoacetophenone (239 mg, 1.2 mmol),[Cp * Ir (6,6 '- (OH) 2bpy) (H2O)] [OTf] 2 (8.3 mg,0.01 mmol, 1 mol%), potassium hydroxide (56 mg, 1.0 mmol, 1.0 equiv.),Aminobenzyl alcohol (123 mg, 1.0 mmol) and water (1 mL) were sequentially added to a 5 mL round bottom flask. It was extracted with ethyl acetate and the reaction mixture was refluxed in air for 12 hours and then cooled to room temperature.Extraction with ethyl acetate, removal of the solvent by rotary evaporation followed by column chromatography (developing solvent: petroleum ether / ethyl acetate) gave the pure target compound in a yield of 86%

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 10160 - 10171
[2]Applied Organometallic Chemistry,2018,vol. 32
[3]Journal of Organic Chemistry,2018,vol. 83,p. 2309 - 2316
[4]Applied Organometallic Chemistry,2019,vol. 33
[5]RSC Advances,2014,vol. 4,p. 52911 - 52914
[6]Organic Letters,2016,vol. 18,p. 3558 - 3561
[7]Patent: CN107400084,2017,A .Location in patent: Paragraph 0056; 0057; 0058
[8]Journal of Organic Chemistry,2019,vol. 84,p. 6286 - 6297
[9]ChemCatChem,2019,vol. 11,p. 4340 - 4350
[10]RSC Advances,2019,vol. 9,p. 28764 - 28767
[11]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3233 - 3238
[12]Chemistry - A European Journal,2019,vol. 25,p. 16099 - 16105
[13]Journal of the American Chemical Society,2011,vol. 133,p. 9878 - 9891
[14]Organic Letters,2019,vol. 21,p. 8065 - 8070
[15]Journal of Organic Chemistry,2019,vol. 84,p. 2626 - 2641
[16]Organic and Biomolecular Chemistry,2018,vol. 16,p. 274 - 284

27
[ 5344-90-1 ]
[ 124676-19-3 ]
[ 1345046-75-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6389 - 6392

28
[ 5344-90-1 ]
[ 1251832-81-1 ]
[ 1428747-35-6 ]

Reference： [1]Molecules,2013,vol. 18,p. 814 - 831

29
[ 5344-90-1 ]
[ 4264-35-1 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 4890 - 4892
[2]Chemical Biology and Drug Design,2015,vol. 85,p. 743 - 755

30
[ 5344-90-1 ]
[ 16619-14-0 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13280 - 13283
Angew. Chem.,2013,vol. 125,p. 13522 - 13525,4

31
[ 5344-90-1 ]
[ 21352-22-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2073 - 2078

32
[ 5344-90-1 ]
[ 4706-43-8 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2003 - 2005

33
[ 5344-90-1 ]
[ 76-05-1 ]
[ 51310-54-4 ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: A 100-mL, three-necked flask equipped with a condenser was charged with Ph3P (2.20 g, 8.4 mmol), Et3N (0.85 g, 8.4 mmol),CBr4 (2.79 g, 8.4 mmol), and fluorine-containing carboxylic acid(2.8 mmol) in toluene (25.0 mL) at 0 C under a nitrogen atmosphereand the solution was then stirred for 10 min. 2-Aminobenzyl alcohol 1 (2.8 mmol) was added to the reaction mixture. Once theaddition was complete, the reaction mixture was heated to reflux for1-3 h. After cooling, the solvent was removed by rotary evaporator,the residue was then carefully washed three times with hexane-EtOAc (4:1), and the precipitate was removed by filtration. The filtratewas combined and concentrated by rotary evaporator. The residue was then purified by column chromatography (hexane-EtOAc,4:1) to give the product.

Reference： [1]Synthesis,2014,vol. 46,p. 3309 - 3314
[2]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1893 - 1896

34
[ 1003-31-2 ]
[ 5344-90-1 ]
2-(thiophene-2-yl)quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With C39H32Cl2N5PRu; potassium tert-butylate; In tert-Amyl alcohol; at 130℃; for 4h;Sealed tube;	General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4.

Reference： [1]Tetrahedron,2019,vol. 75,p. 2697 - 2705
[2]Journal of Organic Chemistry,2019,vol. 84,p. 2626 - 2641
[3]Journal of Organic Chemistry,2018,vol. 83,p. 11154 - 11166
[4]Green Chemistry,2017,vol. 19,p. 2945 - 2951
[5]Organic Letters,2014,vol. 16,p. 6028 - 6031

35
[ 5735-41-1 ]
[ 5344-90-1 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 2545 - 2553

36
[ 5344-90-1 ]
[ 109-86-4 ]
[ 6931-17-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9570 - 9574

37
[ 5344-90-1 ]
[ 5391-88-8 ]
[ 24641-31-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With [Co(N,N'-bis(alpha-pyridyl)-2,6-diaminopyridine)Cl2]; sodium hydroxide; In toluene; at 120℃; for 24h;Inert atmosphere; Molecular sieve; Schlenk technique;	General procedure: Under an N2 atmosphere, a mixture of secondary alcohol (0.5 mmol) and 2-aminobenzyl alcohols (0.6 mmol), 1a (5 mol %),NaOH (0.1 mmol), 4 A molecular sieve (0.6 g), and toluene (1.5 mL) was added into a 25 mL Schlenk tube equipped with a stirring bar.The mixture was heated to 120 C under a steady and slow N2 flow for 24 h. After cooling to ambient temperature, 6 mL water was added and the aqueous solution extracted with ethyl acetate (3 x 5 mL). The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product purified on a short flash chromatography column.

Reference： [1]ChemSusChem,2019,vol. 12,p. 3078 - 3082
[2]ChemCatChem,2019,vol. 11,p. 2500 - 2510
[3]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9570 - 9574
[4]Chemistry - A European Journal,2019,vol. 25,p. 6439 - 6446
[5]Green Chemistry,2019,vol. 21,p. 5345 - 5351
[6]Advanced Synthesis and Catalysis,2018,vol. 360,p. 722 - 729
[7]Tetrahedron,2019,vol. 75
[8]Journal of Catalysis,2019,vol. 373,p. 93 - 102
[9]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3567 - 3574
[10]Organic and Biomolecular Chemistry,2018,vol. 16,p. 274 - 284
[11]Chemistry - A European Journal,2014,vol. 20,p. 13279 - 13285

38
[ 5344-90-1 ]
[ 13228-40-5 ]

Reference： [1]Patent: US2015/315143,2015,A1

39
[ 5344-90-1 ]
[ 34841-35-5 ]
(+)-cis-2-(3-chlorophenyl)-3-methyl-1,2,3,4-tetrahydroquinoline [ No CAS ]
C₁₆H₁₆ClN [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 6266 - 6269

40
[ 5344-90-1 ]
[ 34841-35-5 ]
2-(3-chlorophenyl)-3-methylquinoline [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 6266 - 6269

41
[ 5344-90-1 ]
[ 711-33-1 ]
(+)-cis-3-methyl-2-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
C₁₇H₁₆F₃N [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 6266 - 6269

42
[ 5344-90-1 ]
[ 711-33-1 ]
3-methyl-2-[4′-(trifluoromethyl)phenyl]quinoline [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 6266 - 6269

43
[ 5344-90-1 ]
[ 24641-31-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 824 - 829

44
[ 5344-90-1 ]
[ 160542-02-9 ]
3-(4-(trifluoromethoxy)phenyl)quinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6563 - 6572

45
[ 5344-90-1 ]
[ 14401-72-0 ]
2-(3,5-dichlorophenyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.5 g	With tris(triphenylphosphine)ruthenium(II) chloride; potassium hydroxide; In toluene; for 10h;Reflux; Dean-Stark;	2-aminobenzylalcohol (6. 0g, 48mmol), 3, 5-dichloro nitroacetophenone (12. 0g, 63. 5mmol), RuCl 2 (PPh 3) 3 (0. 5g, 10mol %), and KOH (2. 4g, 42. 0mmol) to 100 ml of toluene for 10h. Dien-stark trap is used to collect water from the reaction product. The reaction mixture is cooled to room temperature to mainteners, filtered through the gel plug. Products, eluent ethyl acetate glycopeptide Phenylbicyclohexane in 2% by using a further refined. 4. (30% yield) of the product obtained after the 0g column. This product is recrystallized from isopropanol addition. 3. 5g of the desired product is obtained.

Reference： [1]Patent: JP2015/212297,2015,A .Location in patent: Paragraph 0108; 0109

46
[ 5344-90-1 ]
[ 935-13-7 ]
[ 91-56-5 ]
3-(furan-2-yl)-N-(2-(((2-(hydroxymethyl)phenyl)carbamoyl)carbonyl)phenyl)propanamide [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3750 - 3753

47
[ 5344-90-1 ]
[ 766-84-7 ]
[ 1353000-31-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With C39H32Cl2N5PRu; potassium tert-butylate; In tert-Amyl alcohol; at 130℃; for 2h;Sealed tube;	General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4.
63%Chromat.	With cesium hydroxide; In 1,4-dioxane; at 100℃; for 24h;	A tubular reactor was charged with o-aminobenzyl alcohol (0.123 g, 1 mmol),3-Chlorobenzonitrile (1.25 mmol, 1.25 equiv.)And cesium hydroxide (0.149 g, 100 mol%) were placed under direct air flow. The air spheres were connected with each other and heated to 100 C for 24 h.After the completion of the reaction by TLC, the product was isolated by column chromatography, and the yield was 63%.

48
[ 5344-90-1 ]
[ 63624-28-2 ]
C₁₅H₁₇NO₅S [ No CAS ]